p-Toluenesulfonic acid → HCID 54042594, compound

HRID 266352Notes

Reaction equation

HRID 266352 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH:13]([CH2:28][O:29]C2CCCCO2)[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:19][CH:18]=2)=[O:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH:13]([CH2:28][OH:29])[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:19][CH:18]=2)=[O:15])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 19032944HCID 19032944, compound

Product 1

HCID 54042594HCID 54042594, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After (RS)-2-(4-chlorobenzenesulfonylaminomethyl)-N-(4-ethoxycarbonylphenyl)-3-(tetrahydropyran-2-yloxy)propanamide (10.8 mg) was dissolved in methanol (5 ml), the mixture was acidified with p-toluenesulfonic acid to pH less than 4, and the whole was stirred for 2 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate. The resulting solution was washed with saturated NaHCO3 and saturated NaCl and dried over Na2SO4 and concentrated to give (RS)-2-(4-chlorobenzenesulfonylaminomethyl)-N-(4-ethoxycarbonylphenyl)-3-hydroxypropanamide (8.1 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe resulting solution was washed with saturated NaHCO3 and saturated NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4b8388dd1ebd4b20916e34ff28459a3c
Source dataset
uspto-grants-1997_07
Patent number
US05650428

Reaction notes

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